Synthesis of the 6- and 7-hydroxy-5,8-dioxocarbostyrils

George Pettit, Wayne C. Fleming, Kenneth D. Paull

Research output: Contribution to journalArticle

54 Citations (Scopus)

Abstract

Utilizing a condensation reaction between amine I and methyl propiolate to obtain pyridone III followed by reaction with potassium t-butoxide and oxygen in dimethyl sulfoxide, a convenient synthesis of 6-hydroxy-5,8-dioxocarbostyril (V) was achieved. Conversion of 8-hydroxycarbostyril via dinitro (XII) and diamino (XIIIa) intermediates provided the isomeric 7-hydroxy-5,8-dioxocarbostyril (XV). The structures assigned to hydroxyquinones V and XV received support from mass spectral and proton magnetic resonance studies.

Original languageEnglish (US)
Pages (from-to)1089-1092
Number of pages4
JournalJournal of Organic Chemistry
Volume33
Issue number3
StatePublished - 1968

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Pyridones
Condensation reactions
Dimethyl Sulfoxide
Amines
Potassium
Nuclear magnetic resonance
Oxygen

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Pettit, G., Fleming, W. C., & Paull, K. D. (1968). Synthesis of the 6- and 7-hydroxy-5,8-dioxocarbostyrils. Journal of Organic Chemistry, 33(3), 1089-1092.

Synthesis of the 6- and 7-hydroxy-5,8-dioxocarbostyrils. / Pettit, George; Fleming, Wayne C.; Paull, Kenneth D.

In: Journal of Organic Chemistry, Vol. 33, No. 3, 1968, p. 1089-1092.

Research output: Contribution to journalArticle

Pettit, G, Fleming, WC & Paull, KD 1968, 'Synthesis of the 6- and 7-hydroxy-5,8-dioxocarbostyrils', Journal of Organic Chemistry, vol. 33, no. 3, pp. 1089-1092.
Pettit, George ; Fleming, Wayne C. ; Paull, Kenneth D. / Synthesis of the 6- and 7-hydroxy-5,8-dioxocarbostyrils. In: Journal of Organic Chemistry. 1968 ; Vol. 33, No. 3. pp. 1089-1092.
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